AR086036A1 - ETHYLLY DERIVATIVES AS POSITIVE ALLOSTERIC MODULATORS OF (mGluR5) - Google Patents
ETHYLLY DERIVATIVES AS POSITIVE ALLOSTERIC MODULATORS OF (mGluR5)Info
- Publication number
- AR086036A1 AR086036A1 ARP120101405A AR086036A1 AR 086036 A1 AR086036 A1 AR 086036A1 AR P120101405 A ARP120101405 A AR P120101405A AR 086036 A1 AR086036 A1 AR 086036A1
- Authority
- AR
- Argentina
- Prior art keywords
- hydrogen
- lower alkyl
- mglur5
- positive allosteric
- allosteric modulators
- Prior art date
Links
- 230000003281 allosteric effect Effects 0.000 title abstract 2
- 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 title 1
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 102000016193 Metabotropic glutamate receptors Human genes 0.000 abstract 2
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 abstract 2
- 229910052736 halogen Chemical group 0.000 abstract 2
- 150000002367 halogens Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 208000010877 cognitive disease Diseases 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 201000000980 schizophrenia Diseases 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
- Y02T10/00—Road transport of goods or passengers
- Y02T10/60—Other road transportation technologies with climate change mitigation effect
- Y02T10/70—Energy storage systems for electromobility, e.g. batteries
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Addiction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Steroid Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Liquid Crystal Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Secondary Cells (AREA)
Abstract
La presente se refiere a derivados de etinilo de la fórmula (1) en la que: X es N o C-R, dicho R es hidrógeno o halógeno; G es N o CH; con la condición de que como máximo uno de G o X pueda ser nitrógeno; R1 es fenilo o piridinilo, que están opcionalmente sustituidos por halógeno; R2 es hidrógeno, alquilo inferior, hidroxi, alcoxi inferior o C(O)O-bencilo; R3, R3’, R4, R4’, R6, R6’ con independencia entre sí son hidrógeno o alquilo inferior; o R6 y R4 junto con el átomo de carbono al que están unidos pueden formar un anillo cicloalquilo C4-6, si m es el número 0 y n es el número 1 ó 2; R5 es hidrógeno o alquilo inferior; n es el número 0, 1 ó 2; m es el número 0 ó 1; con la condición de que n y m no sean simultáneamente el número 0; o a una sal de adición de ácido farmacéuticamente aceptable, a una mezcla racémica, o a su enantiómero correspondiente y/o isómero óptico y/o estereoisómero de los mismos. Ahora se ha encontrado de modo sorprendente que los compuestos de la fórmula general (1) son moduladores alostéricos positivos (PAM) del receptor de glutamato metabotrópico del subtipo 5 (mGluR5). Pueden utilizarse para el tratamiento de la esquizofrenia o de trastornos cognitivos.This refers to ethynyl derivatives of the formula (1) in which: X is N or C-R, said R is hydrogen or halogen; G is N or CH; with the proviso that at most one of G or X can be nitrogen; R1 is phenyl or pyridinyl, which are optionally substituted by halogen; R2 is hydrogen, lower alkyl, hydroxy, lower alkoxy or C (O) O-benzyl; R3, R3 ’, R4, R4’, R6, R6 ’independently of each other are hydrogen or lower alkyl; or R6 and R4 together with the carbon atom to which they are attached can form a C4-6 cycloalkyl ring, if m is the number 0 and n is the number 1 or 2; R5 is hydrogen or lower alkyl; n is the number 0, 1 or 2; m is the number 0 or 1; with the proviso that n and m are not simultaneously the number 0; or to a pharmaceutically acceptable acid addition salt, to a racemic mixture, or to its corresponding enantiomer and / or optical isomer and / or stereoisomer thereof. It has now been surprisingly found that the compounds of the general formula (1) are positive allosteric modulators (PAM) of the subbotot 5 metabotropic glutamate receptor (mGluR5). They can be used for the treatment of schizophrenia or cognitive disorders.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11163683 | 2011-04-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR086036A1 true AR086036A1 (en) | 2013-11-13 |
Family
ID=46025665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP120101405 AR086036A1 (en) | 2011-04-26 | 2012-04-24 | ETHYLLY DERIVATIVES AS POSITIVE ALLOSTERIC MODULATORS OF (mGluR5) |
Country Status (33)
| Country | Link |
|---|---|
| US (2) | US8957213B2 (en) |
| EP (1) | EP2702051B1 (en) |
| JP (1) | JP5753627B2 (en) |
| KR (1) | KR101554803B1 (en) |
| CN (1) | CN103492373B (en) |
| AR (1) | AR086036A1 (en) |
| AU (1) | AU2012247653B2 (en) |
| BR (1) | BR112013026116A2 (en) |
| CA (1) | CA2829170C (en) |
| CL (1) | CL2013003056A1 (en) |
| CO (1) | CO6801734A2 (en) |
| CR (1) | CR20130475A (en) |
| CY (1) | CY1116391T1 (en) |
| DK (1) | DK2702051T3 (en) |
| EA (1) | EA022019B1 (en) |
| ES (1) | ES2534090T3 (en) |
| HR (1) | HRP20150555T1 (en) |
| HU (1) | HUE025031T2 (en) |
| IL (1) | IL228835A (en) |
| MA (1) | MA35133B1 (en) |
| MX (1) | MX337443B (en) |
| MY (1) | MY163164A (en) |
| PE (1) | PE20141169A1 (en) |
| PH (1) | PH12013501895A1 (en) |
| PL (1) | PL2702051T3 (en) |
| PT (1) | PT2702051E (en) |
| RS (1) | RS53903B1 (en) |
| SG (1) | SG194120A1 (en) |
| SI (1) | SI2702051T1 (en) |
| TW (2) | TW201306355A (en) |
| UA (1) | UA110378C2 (en) |
| WO (1) | WO2012146551A1 (en) |
| ZA (1) | ZA201306586B (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG194120A1 (en) * | 2011-04-26 | 2013-11-29 | Hoffmann La Roche | Ethynyl derivatives as positive allosteric modulators of the mglur5 |
| UA110862C2 (en) * | 2011-10-07 | 2016-02-25 | Ф. Хоффманн-Ля Рош Аг | Ethinyl derivatives as allosteric modulators of metabotropic glutamate receptor 5 mglur |
| DK2875000T3 (en) * | 2012-07-17 | 2016-10-24 | Hoffmann La Roche | ARYLETHYNYL DERIVATIVES |
| EP2909178B1 (en) * | 2012-10-18 | 2016-10-05 | F. Hoffmann-La Roche AG | Ethynyl derivatives as modulators of mglur5 receptor activity |
| UA116023C2 (en) * | 2013-07-08 | 2018-01-25 | Ф. Хоффманн-Ля Рош Аг | Ethynyl derivatives as metabotropic glutamate receptor antagonists |
| JP6603334B2 (en) * | 2015-06-03 | 2019-11-06 | エフ．ホフマン−ラ ロシュ アーゲー | Ethynyl derivatives |
| MA42442B1 (en) | 2015-07-15 | 2019-07-31 | Hoffmann La Roche | Ethynyl derivatives as modulators of the metabotropic glutamate receptor |
| US10423423B2 (en) | 2015-09-29 | 2019-09-24 | International Business Machines Corporation | Efficiently managing speculative finish tracking and error handling for load instructions |
| MA45665B1 (en) | 2016-07-18 | 2020-11-30 | Hoffmann La Roche | Ethynyl derivatives |
| JP2020536898A (en) * | 2017-10-10 | 2020-12-17 | バイオジェン インコーポレイテッド | Process for preparing spiro derivatives |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI292318B (en) | 2003-03-10 | 2008-01-11 | Hoffmann La Roche | Imidazol-4-yl-ethynyl-pyridine derivatives |
| GB0325956D0 (en) | 2003-11-06 | 2003-12-10 | Addex Pharmaceuticals Sa | Novel compounds |
| JP5635727B2 (en) * | 2004-10-07 | 2014-12-03 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | Thiazolyl MGLUR5 antagonists and methods for their use |
| WO2006048771A1 (en) | 2004-11-04 | 2006-05-11 | Addex Pharmaceuticals Sa | Novel tetrazole derivatives as positive allosteric modulators of metabotropic glutamate receptors |
| GB0510139D0 (en) | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B1 |
| AU2007267183B2 (en) | 2006-05-31 | 2011-10-20 | F. Hoffmann-La Roche Ag | Aryl-4-ethynyl-isoxazole derivatives |
| CA2689282A1 (en) * | 2007-06-03 | 2008-12-11 | Vanderbilt University | Benzamide mglur5 positive allosteric modulators and methods of making and using same |
| US8034806B2 (en) * | 2007-11-02 | 2011-10-11 | Vanderbilt University | Bicyclic mGluR5 positive allosteric modulators and methods of making and using same |
| CA2734487A1 (en) | 2008-08-20 | 2010-02-25 | Southern Research Institute | Ethynyl-substituted pyridine and pyrimidine derivatives and their use in treating viral infections |
| US8586581B2 (en) | 2009-12-17 | 2013-11-19 | Hoffmann-La Roche Inc | Ethynyl compounds useful for treatment of CNS disorders |
| US8420661B2 (en) | 2010-04-13 | 2013-04-16 | Hoffmann-La Roche Inc. | Arylethynyl derivatives |
| SG194120A1 (en) * | 2011-04-26 | 2013-11-29 | Hoffmann La Roche | Ethynyl derivatives as positive allosteric modulators of the mglur5 |
-
2012
- 2012-04-23 SG SG2013074810A patent/SG194120A1/en unknown
- 2012-04-23 UA UAA201313475A patent/UA110378C2/en unknown
- 2012-04-23 ES ES12718153.5T patent/ES2534090T3/en active Active
- 2012-04-23 PH PH1/2013/501895A patent/PH12013501895A1/en unknown
- 2012-04-23 SI SI201230199T patent/SI2702051T1/en unknown
- 2012-04-23 CA CA2829170A patent/CA2829170C/en not_active Expired - Fee Related
- 2012-04-23 EA EA201391537A patent/EA022019B1/en not_active IP Right Cessation
- 2012-04-23 CN CN201280019903.3A patent/CN103492373B/en not_active Expired - Fee Related
- 2012-04-23 EP EP20120718153 patent/EP2702051B1/en active Active
- 2012-04-23 HU HUE12718153A patent/HUE025031T2/en unknown
- 2012-04-23 PE PE2013002401A patent/PE20141169A1/en active IP Right Grant
- 2012-04-23 MX MX2013011105A patent/MX337443B/en active IP Right Grant
- 2012-04-23 BR BR112013026116A patent/BR112013026116A2/en not_active IP Right Cessation
- 2012-04-23 WO PCT/EP2012/057335 patent/WO2012146551A1/en not_active Ceased
- 2012-04-23 DK DK12718153T patent/DK2702051T3/en active
- 2012-04-23 MY MYPI2013003846A patent/MY163164A/en unknown
- 2012-04-23 RS RS20150192A patent/RS53903B1/en unknown
- 2012-04-23 PL PL12718153T patent/PL2702051T3/en unknown
- 2012-04-23 HR HRP20150555TT patent/HRP20150555T1/en unknown
- 2012-04-23 JP JP2014506826A patent/JP5753627B2/en not_active Expired - Fee Related
- 2012-04-23 KR KR1020137031119A patent/KR101554803B1/en not_active Expired - Fee Related
- 2012-04-23 AU AU2012247653A patent/AU2012247653B2/en not_active Ceased
- 2012-04-23 US US13/452,973 patent/US8957213B2/en active Active
- 2012-04-23 PT PT127181535T patent/PT2702051E/en unknown
- 2012-04-24 TW TW101114538A patent/TW201306355A/en unknown
- 2012-04-24 AR ARP120101405 patent/AR086036A1/en unknown
- 2012-04-24 TW TW101114577A patent/TWI436993B/en not_active IP Right Cessation
-
2013
- 2013-08-29 CO CO13205214A patent/CO6801734A2/en active IP Right Grant
- 2013-09-02 ZA ZA2013/06586A patent/ZA201306586B/en unknown
- 2013-09-23 CR CR20130475A patent/CR20130475A/en unknown
- 2013-10-10 IL IL228835A patent/IL228835A/en active IP Right Grant
- 2013-10-22 CL CL2013003056A patent/CL2013003056A1/en unknown
- 2013-11-22 MA MA36462A patent/MA35133B1/en unknown
-
2015
- 2015-01-06 US US14/590,530 patent/US9212171B2/en active Active
- 2015-05-20 CY CY20151100452T patent/CY1116391T1/en unknown
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